Pyridine → 1-(t-Butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone

HRID 1719901Notes

Reaction equation

HRID 1719901 reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:15])[CH3:14])[CH2:10][C:9]1=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([O:15][C:23](=[O:25])[CH3:24])[CH3:14])[CH2:10][C:9]1=[O:16])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 143289891-(t-Butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone

Product 1

HCID 143289901-(t-Butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(t-butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone (2.46 g) is dissolved in 20 ml CH2Cl2 cooled to 0° and treated with 0.90 g pyridine and 0.080 g of acetyl chloride (added dropwise). The reaction mixture is stirred at 0° for 15 min, allowed to warm to r.t. during the next 15 min and then worked up by dilution with CH2Cl2 and washing with water, drying and evaporating. The residue on chromatography on silica gel gives 1-(t-butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone.

Workup

  1. temperaturecooled to 0°
  2. additionadded dropwise)
  3. washwashing with water
  4. customdrying
  5. customevaporating

Sources & evidence

ORD record
ord-b57c2f2017644d44a334d584bcd9f82b
Source dataset
uspto-grants-1985_09
Patent number
US04543257

Reaction notes

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